Synthesis of 3-alkyl-5-arylamino-6,11-dihydro-3H-anthra[1,2-d]-[1,2,3] triazole-6,11-dione 2-oxides by nitrosation of 3-alkylamino-5-arylamino-6H- anthra[1,9-cd]isoxazol-6-ones

Article abstract of DOI:10.1134/S1070428006090193

Nitrosation of 3-alkylamino-5-arylamino-6H-anthra[1,9-cd]isoxazol-6-ones with sodium nitrite in acetic acid leads to the formation of the corresponding unstable N-nitroso derivatives which are converted into 3-alkyl-5-arylamino-6, 11-dihydro-3H-anthra[1,2

Full text of DOI:10.1134/S1070428006090193

6\QWKHVLVꢀRIꢀꢁꢂ$ON\OꢂꢃꢂDU\ODPLQRꢂꢄꢅꢆꢆꢂGLK\GURꢂꢁ+ꢂDQWKUD>ꢆꢅꢇꢂG@ꢂ
>ꢆꢅꢇꢅꢁ@WULD]ROHꢂꢄꢅꢆꢆꢂGLRQHꢀꢇꢂ2[LGHVꢀE\ꢀ1LWURVDWLRQꢀRIꢀꢁꢂ$ON\Oꢂ
DPLQRꢂꢃꢂDU\ODPLQRꢂꢄ+ꢂDQWKUD>ꢆꢅꢈꢂFG@LVR[D]ROꢂꢄꢂRQHVꢀ
/ꢉꢀ0ꢉꢀ*RUQRVWDHYꢅꢀꢀ/ꢉꢀ9ꢉꢀ'ROJXVKLQDꢅꢀꢀ1ꢉꢀ*ꢉꢀ7LWRYDꢅꢀꢀ(ꢉꢀ9ꢉꢀ$UQRO¶GꢅꢀꢀDQGꢀꢀ7ꢉꢀ,ꢉꢀ/DYULNRYDꢀꢀ
$VWDI¶HYꢀ.UDVQR\DUVNꢀ6WDWHꢀ3HGDJRJLFDOꢀ8QLYHUVLW\ꢁꢀXOꢂꢀ/HEHGHYRLꢀꢃꢄꢁꢀ.UDVQR\DUVNꢁꢀꢅꢅꢆꢆꢇꢄꢀ5XVVLDꢀꢀ
HꢈPDLOꢉꢀJRUQRVWDHY#NVSXꢂUXꢄ
5HFHLYHGꢄ-XO\ꢄꢀꢅꢆꢄꢅꢇꢇꢈꢄ
$EVWUDFW²1LWURVDWLRQꢄRIꢄꢁꢉDON\ODPLQRꢉꢈꢉDU\ODPLQRꢉꢂ+ꢉDQWKUD>ꢀꢆꢊꢉFG@LVR[D]ROꢉꢂꢉRQHVꢄ ZLWKꢄ VRGLXPꢄQLWULWHꢄLQꢄ
DFHWLFꢄDFLGꢄOHDGVꢄWRꢄWKHꢄIRUPDWLRQꢄRIꢄWKHꢄFRUUHVSRQGLQJꢄXQVWDEOHꢄ1ꢉQLWURVRꢄGHULYDWLYHVꢄZKLFKꢄDUHꢄFRQYHUWHGꢄLQWRꢄ
ꢁꢉDON\OꢉꢈꢉDU\ODPLQRꢉꢂꢆꢀꢀꢉGLK\GURꢉꢁ+ꢉDQWKUD>ꢀꢆꢅꢉG@>ꢀꢆꢅꢆꢁ@WULD]ROHꢉꢂꢆꢀꢀꢉGLRQHꢄꢅꢉR[LGHVꢄRQꢄKHDWLQJꢋꢄ
'2,ꢊꢄꢀꢇꢋꢀꢀꢁꢃꢎ6ꢀꢇꢏꢇꢃꢅꢐꢇꢇꢂꢇꢊꢇꢀꢊꢁꢄ
,Wꢄ LVꢄ NQRZQꢄ WKDWꢄ ꢂ+ꢉDQWKUD>ꢀꢆꢊꢉFG@LVR[D]ROHVꢄ SRVꢉ
:HꢄKDYHꢄIRXQGꢄWKDWꢄꢁꢉDON\ODPLQRꢉꢈꢉDU\ODPLQRꢉꢂ+ꢉ
VHVVLQJꢄ YDULRXVꢄ VXEVWLWXHQWVꢄ LQꢄ WKHꢄ ꢁꢉSRVLWLRQꢄ DUHꢄ DQWKUD>ꢀꢆꢊꢉFG@LVR[D]ROꢉꢂꢉRQHVꢄ ,D±,Hꢄ UHDGLO\ꢄ XQGHUJRꢄ
FDSDEOHꢄRIꢄXQGHUJRLQJꢄLVRPHUL]DWLRQꢄLQWRꢄGHULYDWLYHVꢄRIꢄ QLWURVDWLRQꢄZLWKꢄVRGLXPꢄQLWULWHꢄLQꢄDFHWLFꢄDFLGꢄDQGꢄWKDWꢄ
ꢊꢆꢀꢇꢉDQWKUDTXLQRQHꢄ IXVHGꢄ DWꢄWKHꢄꢀꢆꢅꢉSRVLWLRQVꢄ ZLWKꢄꢄ WKHꢄ SULPDU\ꢄ SURGXFWVꢆꢄ ꢁꢉDON\OꢌQLWURVRꢍDPLQRꢉꢈꢉDU\Oꢉ
Dꢄ ILYHꢉꢄ RUꢄ VL[ꢉPHPEHUHGꢄ QLWURJHQꢉFRQWDLQLQJꢄ ULQJꢄ DPLQRꢉꢂ+ꢉDQWKUD>ꢀꢆꢊꢉFG@LVR[D]ROꢉꢂꢉRQHVꢄ ,,D±,,Hꢆꢄ DUHꢄ
ꢌ6FKHPHꢄꢀꢍꢋꢄ7KHVHꢄLVRPHUL]DWLRQVꢄFDQꢄEHꢄSURPRWHGꢄE\ꢄ FRQYHUWHGꢄLQWRꢄQHZꢄFRPSRXQGVꢋꢄ2QꢄWKHꢄEDVLVꢄRIꢄWKHꢄ
KHDWLQJꢆꢄLUUDGLDWLRQꢆꢄRUꢄWUHDWPHQWꢄZLWKꢄEDVHVꢄ>ꢀ±ꢃ@ꢋꢄ,Qꢄ 89ꢆꢄ105ꢆꢄDQGꢄPDVVꢄVSHFWUDꢆꢄWKHꢄILQDOꢄSURGXFWVꢄZHUHꢄ
VRPHꢄFDVHVꢆꢄWKHꢄSURFHVVꢄLVꢄDFFRPSDQLHGꢄE\ꢄSURIRXQGꢄ DVVLJQHGꢄ WKHꢄ VWUXFWXUHꢄ RIꢄ ꢁꢉDON\OꢉꢈꢉDU\ODPLQRꢉꢂꢆꢀꢀꢉ
FKDQJHꢄRIꢄFRORUꢆꢄVRꢄWKDWꢄWKHꢄLQLWLDOꢄFRPSRXQGVꢄPD\ꢄEHꢄ GLK\GURꢉꢁ+ꢉDQWKUD>ꢀꢆꢅꢉG@>ꢀꢆꢅꢆꢁ@WULD]ROꢉꢂꢆꢀꢀꢉGLRQHꢄꢄ
XVHGꢄDVꢄWKHUPDOꢄLQGLFDWRUVꢄ>ꢈ@ꢋꢄ:HꢄEHOLHYHGꢄLWꢄWRꢄEHꢄ ꢅꢉR[LGHVꢄ,,,D±,,,Hꢄꢌ6FKHPHꢄꢅꢍꢋꢄ,QWHUPHGLDWHꢄ1ꢉQLWURVRꢄ
DSSURSULDWHꢄWRꢄVHDUFKꢄIRUꢄVXFKꢄꢂ+ꢉDQWKUD>ꢀꢆꢊꢉFG@LVRꢉ
FRPSRXQGVꢄ,,D±,,HꢄWXUQHGꢄRXWꢄWRꢄEHꢄXQVWDEOHꢄXQGHUꢄ
[D]ROHꢄGHULYDWLYHVꢄZKRVHꢄLVRPHUL]DWLRQꢄZRXOGꢄJLYHꢄULVHꢄ FRQGLWLRQVꢄRIꢄFKURPDWRJUDSKLFꢄVHSDUDWLRQꢆꢄDQGꢄZHꢄ
WRꢄKHWHURF\FOLFꢄGHULYDWLYHVꢄRIꢄꢊꢆꢀꢇꢉDQWKUDTXLQRQHꢄWKDWꢄ IDLOHGꢄWRꢄLVRODWHꢄWKHPꢄDVꢄDQDO\WLFDOO\ꢄSXUHꢄVXEVWDQFHVꢋꢄ
DUHꢄGLIILFXOWꢄWRꢄREWDLQꢄE\ꢄRWKHUꢄPHWKRGVꢋꢄ
7KHLUꢄIRUPDWLRQꢄZDVꢄGHWHFWHGꢄE\ꢄ7/&ꢆꢄDVꢄZHOOꢄDVꢄE\ꢄ
6FKHPHꢀꢆꢉꢀ
5ꢄ ꢄ+2ꢆꢄ$U1+ꢑꢄ;ꢄ ꢄ23Kꢆꢄ63Kꢆꢄ6H3Kꢋꢄ
ꢀꢁꢂꢃꢄ

6<17+(6,6ꢄꢄ2)ꢄꢄꢁꢉ$/.</ꢉꢈꢉ$5</$0,12ꢉꢂꢆꢀꢀꢉ',+<'52ꢉꢋꢋꢋꢄ
ꢀꢁꢂꢈꢄ
6FKHPHꢀꢇꢉꢀ
5ꢄ ꢄLꢉ%XꢄꢌDꢆꢄGꢍꢆꢄ(WꢄꢌEꢆꢄFꢍꢆꢄ%XꢄꢌHꢍꢑꢄ5ꢒꢄ ꢄ+ꢄꢌDꢍꢆꢄꢃꢉ0HꢄꢌEꢆꢄHꢍꢆꢄꢁꢉ0HꢄꢌFꢆꢄGꢍꢋꢄ
VSHFWURSKRWRPHWU\ꢋꢄ)RUꢄH[DPSOHꢆꢄWKHꢄ89ꢄVSHFWUXPꢄRIꢄ
,QꢄWKHꢄPDVVꢄVSHFWUXPꢄRIꢄWULD]ROHꢄ1ꢉR[LGHꢄ,,,EꢆꢄWKHꢄ
WKHꢄUHDFWLRQꢄPL[WXUHꢄREWDLQHGꢄE\ꢄQLWURVDWLRQꢄRIꢄFRPꢉ PRVWꢄDEXQGDQWꢄLRQVꢄZHUHꢄ>0@ ꢄꢌPꢎ]ꢄꢁꢊꢐꢍꢄDQGꢄ>0ꢄ±ꢄꢁꢇ@ ꢆꢄ
SRXQGꢄ ,Eꢄ FRQWDLQHGꢄ ORQJꢉZDYHꢄ DEVRUSWLRQꢄ PD[LPDꢄ DWꢄꢄ WKHꢄODWWHUꢄUHVXOWLQJꢄIURPꢄHOLPLQDWLRQꢄRIꢄWKHꢄ12ꢄJURXSꢋꢄ
ꢄ ꢈꢀꢈꢄ DQGꢄ ꢈꢃꢇꢄ QPꢆꢄ ZKRVHꢄ SRVLWLRQꢄ DOPRVWꢄ FRLQFLGHGꢄ ,QꢄDGGLWLRQꢆꢄDQꢄLRQꢄSHDNꢄZLWKꢄPꢎ]ꢄꢁꢐꢅꢄZDVꢄSUHVHQWꢄGXHꢄ
ZLWKꢄWKHꢄDEVRUSWLRQꢄPD[LPDꢄRIꢄꢈꢉDU\ODPLQRꢉꢁꢉEURPRꢉ
ꢂ+ꢉDQWKUD>ꢀꢆꢊꢉFG@LVR[D]ROꢉꢂꢉRQHVꢄꢌ ꢄꢈꢀꢈꢆꢄꢈꢁꢈꢄQPꢍꢋꢄ Pꢎ]ꢄꢁꢃꢇꢄ DQGꢄ ꢁꢈꢃꢄDUHꢄOLNHO\ꢄ WRꢄ EHꢄ IRUPHGꢄE\ꢄ GHFDUꢉ
7DNLQJꢄ LQWRꢄ DFFRXQWꢄ VLP LODUꢄ HIIHFWVꢄ RIꢄ EURP LQHꢄ DWRP ꢄ ERQ\ODWLRQꢄRIꢄWKHꢄSULPDU\ꢄIUDJPHQWꢄLRQVꢄZLWKꢄPꢎ]ꢄꢁꢂꢐꢄ
DQGꢄ 1ꢉQLWURVRDON\ODPLQRꢄ JURXSꢄ RQꢄ FKURPRSKRUHꢄ V\Vꢉ DQGꢄꢁꢐꢅꢋꢄ$ꢄVWURQJꢄSHDNꢄZLWKꢄPꢎ]ꢄꢊꢀꢄFRUUHVSRQGVꢄWRꢄWKHꢄ
WHPVꢆꢄWKLVꢄIDFWꢄDOVRꢄLQGLFDWHVꢄWKHꢄVLWHꢄRIꢄQLWURVDWLRQꢋꢄ7KHꢄ >& + @ ꢄLRQꢄRULJLQDWLQJꢄIURPꢄWKHꢄꢃꢉPHWK\OSKHQ\ODPLQRꢄ
WRꢄGHR[\JHQDWLRQꢄRIꢄWKHꢄPROHFXODUꢄLRQꢋꢄ,RQVꢄZLWKꢄꢄ
KHWHURF\FOL]DWLRQꢄ RIꢄ 1ꢉQLWURVRꢄ FRPSRXQGVꢄ ,,D±,,Hꢄ WRꢄ
WULD]ROHꢄ1ꢉR[LGHVꢄ,,,D±,,,HꢄZDVꢄFRPSOHWHGꢄE\ꢄKHDWLQJꢄ
WKHꢄUHDFWLRQꢄPL[WXUHꢄREWDLQHGꢄDIWHUꢄQLWURVDWLRQꢄIRUꢄꢅꢇ±
ꢁꢇꢄPLQꢄDWꢄꢈꢇ±ꢏꢇƒ&ꢋꢄꢄ
IUDJPHQWꢋꢄ
7KHꢄWUDQVIRUPDWLRQꢄ,, ,,,ꢆꢄDVꢄZHOOꢄDVꢄWKHꢄF\FOL]Dꢉ
WLRQꢄ RIꢄ ꢅꢉD]LGRꢉꢁꢉDON\OꢌQLWURVRꢍDPLQRꢍꢉꢀꢆꢃꢉQDSKWKRꢉ
TXLQRQHVꢄ WRꢄ ꢀꢉDON\OꢉꢃꢆꢊꢉGLK\GURꢉꢀ+ꢉQDSKWKR>ꢅꢆꢁꢉG@ꢉ
7KHꢄ 89ꢄ VSHFWUDꢄ RIꢄ FRPSRXQGVꢄ ,,,D±,,,Hꢄ LQꢄ WKHꢄ >ꢀꢆꢅꢆꢁ@WULD]ROHꢉꢃꢆꢊꢉGLRQHꢄꢅꢉR[LGHVꢄGHVFULEHGꢄSUHYLRXVO\ꢄ
YLVLEOHꢄUHJLRQꢄZHUHꢄVLPLODUꢄWRꢄWKRVHꢄRIꢄꢈꢉDU\ODPLQRꢉꢁꢉ >ꢏ@ꢄꢌLWꢄRFFXUVꢄDWꢄꢐꢇƒ&ꢍꢆꢄPD\ꢄLQYROYHꢄLQWHUPHGLDWHꢄ
DU\OꢉꢂꢆꢀꢀꢉGLK\GURꢉꢁ+ꢉDQWKUD>ꢀꢆꢅꢉG@>ꢀꢆꢅꢆꢁ@WULD]ROHꢉ
ꢂꢆꢀꢀꢉGLRQHVꢄ>ꢂ@ꢋꢄ7KHꢄ +ꢄ105ꢄVSHFWUDꢄRIꢄLQLWLDOꢄLVR[Dꢉ
IRUPDWLRQꢄRIꢄQLWUHQHVꢄ,9D±,9Hꢄꢌ6FKHPHꢄꢁꢍꢋꢄ+RZHYHUꢆꢄ
LVRPHUL]DWLRQVꢄW\SLFDOꢄRIꢄꢂ+ꢉDQWKUD>ꢀꢆꢊꢉFG@LVR[D]ROꢉꢂꢉ
]RORDQWKURQHVꢄ,D±,HꢄDQGꢄWULD]ROHꢄ1ꢉR[LGHVꢄ,,,D±,,,Hꢄ RQHVꢄ XVXDOO\ꢄ UHTXLUHꢄ P RUHꢄ VHYHUHꢄ FRQGLWLRQVꢆꢄ QDP HO\ꢄ
GLIIHUꢄPDLQO\ꢄLQꢄWKHꢄSRVLWLRQꢄRIꢄVLJQDOVꢄIURPꢄWKHꢄ KHDWLQJꢄRIꢄWKHꢄVXEVWUDWHVꢄDERYHꢄꢀꢇꢇƒ&ꢄ>ꢀ±ꢁ@ꢋꢄ7KHUHꢉ
DON\OꢄJURXSVꢄRQꢄWKHꢄQLWURJHQꢄDWRPꢄDQGꢄIURPꢄꢃꢉ+ꢋꢄ7KHꢄ IRUHꢆꢄDꢄ FRQFHUWHGꢄSDWKꢄRIꢄ WKHꢄ LVRPHUL]DWLRQꢄ ZLWKRXWꢄ
ꢃꢉ+ꢄVLJQDOꢄLQꢄWKHꢄVSHFWUXPꢄRIꢄ,EꢄDSSHDUVꢄDVꢄDꢄVLQJOHWꢄDWꢄ
ꢄꢂꢋꢀꢈꢄSSPꢆꢄZKLOHꢄWKHꢄFRUUHVSRQGLQJꢄWULD]ROHꢄ1ꢉR[LGHꢄ
,,Eꢄ LVꢄ FKDUDFWHUL]HGꢄ E\ꢄ WKHꢄ ꢃꢉ+ꢄ VLJQDOꢄ ORFDWHGꢄ DWꢄꢄ
ꢄꢂꢋꢊꢀꢄSSPꢑꢄWKHꢄGRZQILHOGꢄVKLIWꢄLVꢄLQGXFHGꢄE\ꢄHOHFWURQꢉ
DFFHSWRUꢄHIIHFWꢄRIꢄWKHꢄWULD]ROHꢄR[LGHꢄPRLHW\ꢋꢄ7KHꢄVDPHꢄ
SDUWLFLSDWLRQꢄRIꢄQLWUHQHꢄVSHFLHVꢄFDQQRWꢄEHꢄUXOHGꢄRXWꢋꢄ
(;3(5,0(17$/ꢄ
7KHꢄ +ꢄ105ꢄVSHFWUDꢄZHUHꢄUHFRUGHGꢄIURPꢄVROXWLRQVꢄ
IDFWRUꢄLVꢄUHVSRQVLEOHꢄIRUꢄWKHꢄGRZQILHOGꢄVKLIWꢄRIꢄVLJQDOVꢄ LQꢄ'062ꢉG ꢄRUꢄ&'&O ꢄRQꢄDꢄ%UXNHUꢄ'5;ꢉꢈꢇꢇꢄVSHFꢉ
IURPꢄSURWRQVꢄRIꢄWKHꢄꢁꢉ&+ ꢄJURXSVꢄLQꢄFRPSRXQGVꢄ,,,ꢆꢄDVꢄ WURPHWHUꢄXVLQJꢄWHWUDPHWK\OVLODQHꢄDVꢄLQWHUQDOꢄUHIHUHQFHꢋꢄ
FRPSDUHGꢄWRꢄLQLWLDOꢄLVR[D]ROHꢄGHULYDWLYHVꢄ,ꢋꢄ
7KHꢄHOHFWURQLFꢄVSHFWUDꢄZHUHꢄPHDVXUHGꢄRQꢄDꢄ+HOLRVꢄ
6FKHPHꢀꢁꢉꢀ
5866,$1ꢄꢄ-2851$/ꢄꢄ2)ꢄꢄ25*$1,&ꢄꢄ&+(0,675<ꢄꢄꢄ9ROꢋꢄꢄꢃꢅꢄꢄꢄ1Rꢋꢄꢄꢊꢄꢄꢄꢅꢇꢇꢂꢄ

*251267$(9ꢄꢄHWꢄDOꢋꢄ
ꢀꢁꢂꢂꢄ
(SVLORQꢄVSHFWURSKRWRPHWHUꢄLQꢄWROXHQHꢄꢌFꢄ ꢄꢀîꢀꢇ ꢄ0ꢍꢄ ꢌꢁꢋꢊꢃꢍꢆꢄꢃꢐꢈꢄꢌꢃꢋꢁꢅꢍꢆꢄꢈꢀꢈꢄꢌꢃꢋꢁꢐꢍꢋꢄ +ꢄ105ꢄVSHFWUXPꢄ
XVLQJꢄꢀꢉFPꢄFHOOVꢋꢄ7KHꢄSURJUHVVꢄRIꢄUHDFWLRQVꢄDQGꢄWKHꢄ ꢌ'062ꢉG ꢍꢆꢄ ꢆꢄSSPꢓꢄꢇꢋꢊꢇꢄVꢄ>ꢂ+ꢆꢄꢌ&+ ꢍ &+@ꢆꢄꢅꢋꢇꢇꢄEUꢋVꢄ
SXULW\ꢄRIꢄSURGXFWVꢄZHUHꢄPRQLWRUHGꢄE\ꢄ7/&ꢄRQꢄ6LOXIROꢄ ꢌꢀ+ꢆꢄ&+ꢍꢆꢄꢅꢋꢃꢇꢄVꢄꢌꢁ+ꢆꢄ&+ & + ꢍꢆꢄꢁꢋꢅꢇꢄEUꢋVꢄꢌꢅ+ꢆꢄ&+ ꢍꢆꢄ
89ꢉꢅꢈꢃꢄSODWHVꢋꢄ7KHꢄPHOWLQJꢄSRLQWVꢄZHUHꢄGHWHUPLQHGꢄRQꢄ ꢂꢋꢅꢈꢄEUꢋVꢄꢌꢀ+ꢆꢄꢃꢉ+ꢍꢆꢄꢏꢋꢀꢇ±ꢏꢋꢃꢇꢄPꢄꢌꢃ+ꢆꢄ& + ꢍꢆꢄꢏꢋꢂꢈ±ꢐꢋꢈꢈꢄ
Dꢄ%RHWLXVꢄPHOWLQJꢄSRLQWꢄDSSDUDWXVꢋꢄ7KHꢄPDVVꢄVSHFWUDꢄ ꢌꢃ+ꢆꢄ+ ꢍꢆꢄꢐꢋꢀꢂꢄGꢄꢌꢀ+ꢆꢄ&+ 1+ꢆꢄ-ꢄ ꢄꢂꢄ+]ꢍꢆꢄꢀꢀꢋꢏꢇꢄVꢄ
ꢌꢀ+ꢆꢄ1+ꢍꢋꢄ)RXQGꢆꢄMꢓꢄ&ꢄꢏꢈꢋꢈꢅꢑꢄ+ꢄꢈꢋꢐꢈꢑꢄ1ꢄꢀꢇꢋꢈꢂꢋꢄ
& + 1 2 ꢋꢄ&DOFXODWHGꢆꢄMꢓꢄ&ꢄꢏꢈꢋꢈꢂꢑꢄ+ꢄꢈꢋꢇꢐꢑꢄ1ꢄꢀꢇꢋꢈꢐꢋꢄꢄ
ZHUHꢄUXQꢄRQꢄDꢄ)LQQLJDQꢄ0$7ꢉꢐꢅꢇꢇꢄLQVWUXPHQWꢋꢄ
ꢁꢂ$ON\ODPLQRꢂꢃꢂDU\ODPLQRꢂꢄ+ꢂDQWKUD>ꢆꢅꢈꢂFG@ꢂ
LVR[D]ROꢂꢄꢂRQHVꢀ,D±,HꢀꢋJHQHUDOꢀSURFHGXUHꢌꢉꢄ7KHꢄFRUUHꢉ
VSRQGLQJꢄDPLQHꢆꢄꢀꢇꢄPPROꢆꢄZDVꢄDGGHGꢄXQGHUꢄVWLUULQJꢄWRꢄ
DꢄVROXWLRQꢄRIꢄꢈꢄPPROꢄRIꢄꢈꢉDU\ODPLQRꢉꢁꢉEURPRꢉꢂ+ꢉ
DQWKUD>ꢀꢆꢊꢉFG@LVR[D]ROꢉꢂꢉRQHꢄLQꢄꢐꢄPOꢄRIꢄ'0)ꢆꢄDQGꢄWKHꢄ
PL[WXUHꢄZDVꢄVWLUUHGꢄIRUꢄꢅꢇ±ꢃꢇꢄPLQꢄDWꢄꢃꢇ±ꢈꢇƒ&ꢄXQWLOꢄWKHꢄ
LQLWLDOꢄUHDFWDQWVꢄGLVDSSHDUHGꢋꢄ7KHꢄPL[WXUHꢄZDVꢄFRROHGꢄ
WRꢄꢈ±ꢀꢇƒ&ꢆꢄDQGꢄWKHꢄSUHFLSLWDWHꢄZDVꢄILOWHUHGꢄRIIꢆꢄZDVKHGꢄ
LQꢄVXFFHVVLRQꢄZLWKꢄꢈ±ꢀꢇꢄPOꢄRIꢄHWKDQROꢆꢄꢀꢇ±ꢀꢈꢄPOꢄRIꢄ
ꢈꢇMꢄ DTXHRXVꢄ HWKDQROꢆꢄ DQGꢄ ꢅꢇ±ꢁꢇꢄ POꢄ RIꢄ ZDWHUꢆꢄ DQGꢄ
UHFU\VWDOOL]HGꢄIURPꢄ'0)ꢄKHDWHGꢄWRꢄꢂꢇƒ&ꢋꢄ
ꢁꢂ%XW\ODPLQRꢂꢃꢂꢋꢍꢂPHWK\OSKHQ\ODPLQRꢌꢂꢄ+ꢂ
DQWKUD>ꢆꢅꢈꢂFG@LVR[D]ROꢂꢄꢂRQHꢀ ꢋ,Hꢌꢉꢄ <LHOGꢄ ꢀꢋꢂꢇꢄ Jꢄ
ꢌꢐꢃMꢍꢆꢄ P Sꢄ ꢀꢊꢇƒ&ꢋꢄ 89ꢄ VSHFWUXP ꢆꢄ
ꢄ ꢌORJ ꢍꢓꢄ ꢁꢊꢈꢄ
ꢌꢁꢋꢊꢅꢍꢆꢄꢃꢐꢈꢄꢌꢃꢋꢁꢁꢍꢆꢄꢈꢀꢈꢄꢌꢃꢋꢁꢊꢍꢋꢄ +ꢄ105ꢄVSHFWUXPꢄ
ꢌ'062ꢉG ꢍꢆꢄ ꢆꢄSSPꢓꢄꢇꢋꢊꢇꢄWꢄꢌꢁ+ꢆꢄ&+ &+ ꢍꢆꢄꢀꢋꢁꢇ±ꢀꢋꢏꢇꢄ
ꢌꢃ+ꢆꢄ &+ ꢍꢆꢄ ꢅꢋꢁꢐꢄ Vꢄ ꢌꢁ+ꢆꢄ &+ & + ꢍꢆꢄ ꢁꢋꢃꢇꢄ EUꢋVꢄ ꢌꢅ+ꢆꢄ
&+ 1ꢍꢆꢄꢂꢋꢀꢈꢄEUꢋVꢄꢌꢀ+ꢆꢄꢃꢉ+ꢍꢆꢄꢏꢋꢅꢈ±ꢏꢋꢃꢇꢄPꢄꢌꢃ+ꢆꢄ& + ꢍꢆꢄ
ꢏꢋꢂꢇ±ꢐꢋꢈꢇꢄꢌꢃ+ꢆꢄ+ ꢍꢆꢄꢐꢋꢁꢈꢄVꢄꢌꢀ+ꢆꢄ&+ 1+ꢍꢆꢄꢀꢀꢋꢏꢇꢄVꢄ
ꢌꢀ+ꢆꢄ1+ꢍꢋꢄ)RXQGꢆꢄMꢓꢄ&ꢄꢏꢈꢋꢈꢅꢑꢄ+ꢄꢈꢋꢐꢈꢑꢄ1ꢄꢀꢇꢋꢈꢂꢋꢄ
& + 1 2 ꢋꢄ&DOFXODWHGꢆꢄMꢓꢄ&ꢄꢏꢈꢋꢈꢂꢑꢄ+ꢄꢈꢋꢇꢐꢑꢄ1ꢄꢀꢇꢋꢈꢐꢋꢄ
ꢁꢂ,VREXW\ODPLQRꢂꢃꢂSKHQ\ODPLQRꢂꢄ+ꢂDQWKUDꢂꢀ
>ꢆꢅꢈꢂFG@LVR[D]ROꢂꢄꢂRQHꢀ ꢋ,Dꢌꢉꢄ <LHOGꢄ ꢀꢋꢂꢈꢄ Jꢄ ꢌꢊꢇMꢍꢆꢄꢄ
ꢁꢂ$ON\OꢂꢃꢂDU\ODPLQRꢂꢄꢅꢆꢆꢂGLK\GURꢂꢁ+ꢂDQWKUDꢂ
>ꢆꢅꢇꢂG@>ꢆꢅꢇꢅꢁ@WULD]ROHꢂꢄꢅꢆꢆꢂGLRQHꢀ ꢇꢂR[LGHVꢀ ,,,D±,,,Hꢀ
ꢋJHQHUDOꢀSURFHGXUHꢌꢉꢄ&RPSRXQGꢄ,D±,HꢆꢄꢅꢈꢄPPROꢆꢄZDVꢄ
GLVVROYHGꢄLQꢄꢅꢇꢄPOꢄRIꢄDFHWLFꢄDFLGꢆꢄDQGꢄꢇꢋꢈ±ꢇꢋꢐꢄJꢄRIꢄ
VRGLXPꢄQLWULWHꢄZDVꢄDGGHGꢄLQꢄVPDOOꢄSRUWLRQVꢄXQGHUꢄ
VWLUULQJꢋꢄ7KHꢄ P L[WXUHꢄ ZDVꢄVWLUUHGꢄIRUꢄ ꢅꢇ±ꢃꢇꢄ P LQꢄ XQWLOꢄ
WKHꢄLQLWLDOꢄFRPSRXQGꢄGLVDSSHDUHGꢆꢄKHDWHGꢄWRꢄꢂꢇ±ꢏꢇƒ&ꢆꢄ
DQGꢄ NHSWꢄ IRUꢄ ꢅꢇ±ꢁꢇꢄ P LQꢄ DWꢄ WKDWꢄ WHP SHUDWXUHꢄ XQWLOꢄꢄ
DꢄEOXH±YLROHWꢄVROLGꢄVHSDUDWHGꢋꢄ7KHꢄPL[WXUHꢄZDVꢄFRROHGꢆꢄ
DQGꢄWKHꢄSUHFLSLWDWHꢄZDVꢄILOWHUHGꢄRIIꢆꢄZDVKHGꢄLQꢄVXFFHVꢉ
VLRQꢄZLWKꢄꢏꢇ±ꢐꢇꢄPOꢄRIꢄZDWHUꢆꢄꢀꢇ±ꢀꢈꢄPOꢄRIꢄꢈꢇMꢄDTXHꢉ
RXVꢄHWKDQROꢆꢄDQGꢄꢈ±ꢀꢇꢄPOꢄRIꢄHWKDQROꢆꢄDQGꢄUHFU\VWDOOL]HGꢄ
IURPꢄSꢉ[\OHQHꢋꢄ
PSꢄ ꢅꢇꢇƒ&ꢋꢄ 89ꢄVSHFWUXPꢆꢄ
ꢄꢌORJ ꢍꢓꢄꢁꢊꢈꢄꢌꢁꢋꢊꢅꢍꢆꢄꢃꢐꢈꢄ
ꢌꢃꢋꢁꢀꢍꢆꢄꢈꢀꢈꢄꢌꢃꢋꢁꢏꢍꢋꢄ +ꢄ105ꢄVSHFWUXPꢄꢌ'062ꢉG ꢍꢆꢄ ꢆꢄ
SSPꢓꢄꢇꢋꢊꢈꢄVꢄꢌꢂ+ꢆꢄ&+ ꢍꢆꢄꢅꢋꢇꢇꢄEUꢋVꢄꢌꢀ+ꢆꢄ&+ꢍꢆꢄꢁꢋꢅꢈꢄꢌꢅ+ꢆꢄ
&+ ꢍꢆꢄꢂꢋꢅꢈꢄEUꢋVꢄꢌꢀ+ꢆꢄꢃꢉ+ꢍꢆꢄꢏꢋꢅꢈ±ꢏꢋꢈꢈꢄPꢄꢌꢈ+ꢆꢄ& + ꢍꢆꢄ
ꢏꢋꢂꢇ±ꢐꢋꢂꢇꢄ Pꢄ ꢌꢃ+ꢆꢄ + ꢍꢆꢄ ꢐꢋꢀꢈꢄ Gꢄ ꢌꢀ+ꢆꢄ &+ 1+ꢆꢄ -ꢄ ꢄꢄ
ꢈꢄ+]ꢍꢆꢄꢀꢀꢋꢏꢈꢄVꢄꢌꢀ+ꢆꢄ1+ꢍꢋꢄ)RXQGꢆꢄMꢓꢄ&ꢄꢏꢈꢋꢇꢊꢑꢄ+ꢄꢈꢋꢃꢏꢑꢄ
1ꢄꢀꢇꢋꢐꢅꢋꢄ& + 1 2 ꢋꢄ&DOFXODWHGꢆꢄMꢓꢄ&ꢄꢏꢈꢋꢀꢊꢑꢄ+ꢄꢈꢋꢃꢐꢑꢄ
1ꢄꢀꢇꢋꢊꢏꢋꢄꢄ
ꢁꢂ(WK\ODPLQRꢂꢃꢂꢋꢍꢂPHWK\OSKHQ\ODPLQRꢌꢂꢄ+ꢂ
DQWKUD>ꢆꢅꢈꢂFG@LVR[D]ROꢂꢄꢂRQHꢀ ꢋ,Eꢌꢉꢄ <LHOGꢄ ꢀꢋꢂꢇꢄ Jꢄ
ꢌꢐꢏMꢍꢆꢄPSꢄꢀꢐꢈ±ꢀꢐꢏƒ&ꢋꢄ89ꢄVSHFWUXPꢆꢄ
ꢄꢌORJ ꢍꢓꢄꢁꢊꢇꢄ
ꢌꢁꢋꢊꢂꢍꢆꢄꢃꢐꢈꢄꢌꢃꢋꢁꢅꢍꢆꢄꢈꢀꢈꢄꢌꢃꢋꢁꢐꢍꢋꢄ +ꢄ105ꢄVSHFWUXPꢄ
ꢌ'062ꢉG ꢍꢆꢄ ꢆꢄSSPꢓꢄꢀꢋꢅꢈꢄWꢄꢌꢁ+ꢆꢄ&+ &+ ꢍꢆꢄꢅꢋꢁꢂꢄVꢄꢌꢁ+ꢆꢄ
&+ & + ꢍꢆꢄꢁꢋꢃꢂꢄEUꢋVꢄꢌꢅ+ꢆꢄ&+ ꢍꢆꢄꢂꢋꢀꢈꢄVꢄꢌꢀ+ꢆꢄꢃꢉ+ꢍꢆꢄ
ꢏꢋꢁꢇ±ꢏꢋꢃꢇꢄPꢄꢌꢃ+ꢆꢄ& + ꢍꢆꢄꢏꢋꢂꢇꢉꢐꢋꢈꢇꢄꢌꢃ+ꢆꢄ+ ꢍꢆꢄꢐꢋꢁꢂꢄVꢄ
ꢌꢀ+ꢆꢄ&+ 1+ꢍꢆꢄꢀꢀꢋꢏꢈꢄVꢄꢌꢀ+ꢆꢄ1+ꢍꢋꢄ)RXQGꢆꢄMꢓꢄ&ꢄꢏꢃꢋꢃꢊꢑꢄ
+ꢄꢈꢋꢀꢊꢑꢄ1ꢄꢀꢀꢋꢃꢀꢋꢄ& + 1 2 ꢋꢄ&DOFXODWHGꢆꢄMꢓꢄ&ꢄꢏꢃꢋꢏꢊꢑꢄ
+ꢄꢈꢋꢀꢈꢑꢄ1ꢄꢀꢀꢋꢁꢐꢋꢄꢄ
ꢁꢂ,VREXW\OꢂꢃꢂSKHQ\ODPLQRꢂꢄꢅꢆꢆꢂGLK\GURꢂꢁ+ꢂ
DQWKUD>ꢆꢅꢇꢂG@>ꢆꢅꢇꢅꢁ@WULD]ROHꢂꢄꢅꢆꢆꢂGLRQHꢀ ꢇꢂR[LGHꢀ
ꢋ,,,Dꢌꢉꢀ <LHOGꢄ ꢇꢋꢏꢄ Jꢄ ꢌꢂꢐMꢍꢆꢄ PSꢄ ꢅꢃꢅ±ꢅꢃꢈƒ&ꢋꢄ 89ꢄ VSHFꢉ
WUXPꢆꢄ
ꢄꢌORJ ꢍꢓꢄꢁꢃꢇꢄꢌꢃꢋꢀꢃꢍꢆꢄꢈꢃꢈꢄꢌꢁꢋꢊꢀꢍꢋꢄ +ꢄ105ꢄ
VSHFWUXPꢄꢌ&'&O ꢍꢆꢄ ꢆꢄSSPꢓꢄꢇꢋꢊꢅꢄGꢄ>ꢂ+ꢆꢄꢌ&+ ꢍ &+ꢆꢄ-ꢄ ꢄ
ꢂꢄ+]@ꢆꢄꢅꢋꢅꢃꢄꢌꢀ+ꢆꢄ&+ꢍꢆꢄꢃꢋꢇꢂꢄGꢄꢌꢅ+ꢆꢄ&+ ꢆꢄ-ꢄ ꢄꢂꢋꢐꢄ+]ꢍꢆꢄ
ꢏꢋꢇꢇꢄVꢄꢌꢀ+ꢆꢄꢃꢉ+ꢍꢆꢄꢏꢋꢅꢇ±ꢏꢋꢈꢄꢌꢈ+ꢆꢄ& + ꢍꢆꢄꢏꢋꢏ±ꢐꢋꢁꢇꢄꢌꢃ+ꢆꢄ
+
ꢍꢆꢄꢀꢀꢋꢈꢇꢄVꢄꢌꢀ+ꢆꢄ1+ꢍꢋꢄ)RXQGꢆꢄMꢓꢄ&ꢄꢂꢊꢋꢃꢅꢑꢄ+ꢄꢃꢋꢂꢐꢑꢄ
ꢁꢂ(WK\ODPLQRꢂꢃꢂꢋꢁꢂPHWK\OSKHQ\ODPLQRꢌꢂꢄ+ꢂ
DQWKUD>ꢆꢅꢈꢂFG@LVR[D]ROꢂꢄꢂRQHꢀ ꢋ,Fꢌꢉꢄ <LHOGꢄ ꢀꢋꢈꢈꢄ Jꢄ
1ꢄꢀꢁꢋꢅꢏꢋꢄ& + 1 2 ꢋꢄ&DOFXODWHGꢆꢄMꢓꢄ&ꢄꢂꢊꢋꢊꢇꢑꢄ+ꢄꢃꢋꢐꢈꢑꢄ
1ꢄꢀꢁꢋꢈꢊꢋꢄꢄ
ꢌꢐꢈMꢍꢆꢄPSꢄꢀꢐꢁ±ꢀꢐꢈƒ&ꢋꢄ89ꢄVSHFWUXPꢆꢄ
ꢄꢌORJ ꢍꢓꢄꢁꢊꢇꢄ
ꢌꢁꢋꢊꢈꢍꢆꢄꢃꢐꢈꢄꢌꢃꢋꢁꢀꢍꢆꢄꢈꢀꢈꢄꢌꢃꢋꢁꢐꢍꢋꢄ +ꢄ105ꢄVSHFWUXPꢄ
ꢌ'062ꢉG ꢍꢆꢄ ꢆꢄSSPꢓꢄꢀꢋꢅꢈꢄWꢄꢌꢁ+ꢆꢄ&+ &+ ꢍꢆꢄꢅꢋꢁꢐꢄVꢄꢌꢁ+ꢆꢄ
&+ & + ꢍꢆꢄꢁꢋꢃꢈꢄEUꢋVꢄꢌꢅ+ꢆꢄ&+ ꢍꢆꢄꢂꢋꢅꢇꢄVꢄꢌꢀ+ꢆꢄꢃꢉ+ꢍꢆꢄ
ꢏꢋꢀꢇ±ꢏꢋꢃꢈꢄPꢄꢌꢃ+ꢆꢄ& + ꢍꢆꢄꢏꢋꢂꢇ±ꢐꢋꢈꢇꢄꢌꢃ+ꢆꢄ+ ꢍꢆꢄꢐꢋꢁꢊꢄVꢄ
ꢌꢀ+ꢆꢄ&+ 1+ꢍꢆꢄꢀꢀꢋꢏꢈꢄVꢄꢌꢀ+ꢆꢄ1+ꢍꢋꢄ)RXQGꢆꢄMꢓꢄ&ꢄꢏꢃꢋꢅꢇꢑꢄ
+ꢄꢈꢋꢀꢁꢑꢄ1ꢄꢀꢀꢋꢇꢂꢋꢄ& + 1 2 ꢋꢄ&DOFXODWHGꢆꢄMꢓꢄ&ꢄꢏꢃꢋꢏꢊꢑꢄ
+ꢄꢈꢋꢀꢈꢑꢄ1ꢄꢀꢀꢋꢁꢐꢋꢄꢄ
ꢁꢂ(WK\OꢂꢃꢂꢋꢍꢂPHWK\OSKHQ\ODPLQRꢌꢂꢄꢅꢆꢆꢂGLK\GURꢂ
ꢁ+ꢂDQWKUD>ꢆꢅꢇꢂG@>ꢆꢅꢇꢅꢁ@WULD]ROHꢂꢄꢅꢆꢆꢂGLRQHꢀ ꢇꢂR[LGHꢀ
ꢋ,,,Eꢌꢉꢄ <LHOGꢄꢇꢋꢂꢄ Jꢄ ꢌꢂꢀMꢍꢆꢄ PSꢄ ꢅꢏꢁ±ꢅꢏꢃƒ&ꢋꢄ 89ꢄ VSHFꢉ
WUXPꢆꢄ
ꢄꢌORJ ꢍꢓꢄꢁꢃꢈꢄꢌꢃꢋꢇꢏꢍꢆꢄꢈꢃꢈꢄꢌꢁꢋꢐꢂꢍꢋꢄ +ꢄ105ꢄ
VSHFWUXPꢄ ꢌ&'&O ꢍꢆꢄ ꢆꢄSSPꢓꢄ ꢀꢋꢁꢈꢄWꢄꢌꢁ+ꢆꢄ &+ &+ ꢍꢆꢄꢄ
ꢅꢋꢃꢇꢄVꢄꢌꢁ+ꢆꢄ&+ & + ꢍꢆꢄꢃꢋꢁꢀꢄTꢄꢌꢅ+ꢆꢄ&+ ꢍꢆꢄꢂꢋꢊꢀꢄVꢄꢌꢀ+ꢆꢄ
ꢃꢉ+ꢍꢆꢄꢏꢋꢇꢈꢄPꢄꢌꢃ+ꢆꢄ& + ꢍꢆꢄꢏꢋꢏꢈ±ꢐꢋꢁꢇꢄꢌꢃ+ꢆꢄ+
ꢍꢆꢄꢄ
ꢀꢀꢋꢃꢇꢄVꢄꢌꢀ+ꢆꢄ1+ꢍꢋꢄ)RXQGꢆꢄMꢓꢄ&ꢄꢂꢊꢋꢀꢀꢑꢄ+ꢄꢃꢋꢃꢀꢑꢄ1ꢄꢀꢃꢋꢇꢅꢋꢄ
ꢁꢂ,VREXW\ODPLQRꢂꢃꢂꢋꢁꢂPHWK\OSKHQ\ODPLQRꢌꢂꢄ+ꢂ
DQWKUD>ꢆꢅꢈꢂFG@LVR[D]ROꢂꢄꢂRQHꢀ ꢋ,Gꢌꢉꢄ <LHOGꢄ ꢀꢋꢏꢈꢄ Jꢄ & + 1 2 ꢋꢄ&DOFXODWHGꢆꢄMꢓꢄ&ꢄꢂꢊꢋꢁꢈꢑꢄ+ꢄꢃꢋꢈꢅꢑꢄ1ꢄꢀꢃꢋꢇꢏꢋꢄ
ꢌꢊꢇMꢍꢆꢄPSꢄꢀꢐꢐ±ꢀꢊꢇƒ&ꢋꢄ89ꢄVSHFWUXPꢆꢄ
ꢄꢌORJ ꢍꢓꢄꢁꢊꢈꢄ 0ꢄꢁꢊꢐꢋꢃꢀꢋꢄ
5866,$1ꢄꢄ-2851$/ꢄꢄ2)ꢄꢄ25*$1,&ꢄꢄ&+(0,675<ꢄꢄꢄ9ROꢋꢄꢄꢃꢅꢄꢄꢄ1Rꢋꢄꢄꢊꢄꢄꢄꢅꢇꢇꢂꢄ

6<17+(6,6ꢄꢄ2)ꢄꢄꢁꢉ$/.</ꢉꢈꢉ$5</$0,12ꢉꢂꢆꢀꢀꢉ',+<'52ꢉꢋꢋꢋꢄ
ꢀꢁꢂꢏꢄ
ꢌꢅ+ꢆꢄ&+ 1ꢍꢆꢄꢏꢋꢅꢇꢄVꢄꢌꢀ+ꢆꢄꢃꢉ+ꢍꢆꢄꢏꢋꢅꢇ±ꢏꢋꢃꢇꢄꢌꢃ+ꢆꢄ& + ꢍꢆꢄ
ꢏꢋꢏꢇ±ꢐꢋꢃꢇꢄꢌꢃ+ꢆꢄ+ ꢍꢆꢄꢀꢀꢋꢃꢈꢄVꢄꢌꢀ+ꢆꢄ1+ꢍꢋꢄ)RXQGꢆꢄMꢓꢄꢄ
&ꢄꢂꢊꢋꢊꢅꢑꢄ+ꢄꢃꢋꢊꢈꢑꢄ1ꢄꢀꢅꢋꢂꢀꢋꢄ& + 1 2 ꢋꢄ&DOFXODWHGꢆꢄMꢓꢄ
&ꢄꢏꢇꢋꢃꢅꢑꢄ+ꢄꢈꢋꢀꢂꢑꢄ1ꢄꢀꢁꢋꢀꢈꢋꢄ
ꢁꢂ(WK\OꢂꢃꢂꢋꢁꢂPHWK\OSKHQ\ODPLQRꢌꢂꢄꢅꢆꢆꢂGLK\GURꢂ
ꢁ+ꢂDQWKUD>ꢆꢅꢇꢂG@>ꢆꢅꢇꢅꢁ@WULD]ROHꢂꢄꢅꢆꢆꢂGLRQHꢀ ꢇꢂR[LGHꢀ
ꢋ,,,Fꢌꢉꢀ <LHOGꢄ ꢇꢋꢏꢄ Jꢄ ꢌꢏꢇMꢍꢆꢄ PSꢄ ꢅꢅꢃ±ꢅꢅꢂƒ&ꢋꢄ 89ꢄ VSHFꢉ
WUXPꢆꢄ
ꢄꢌORJ ꢍꢓꢄꢁꢃꢇꢄꢌꢃꢋꢇꢂꢍꢆꢄꢈꢃꢈꢄꢌꢁꢋꢏꢊꢍꢋꢄ +ꢄ105ꢄ
VSHFWUXPꢄ ꢌ&'&O ꢍꢆꢄ ꢆꢄSSPꢓꢄ ꢀꢋꢁꢈꢄWꢄꢌꢁ+ꢆꢄ &+ &+ ꢍꢆꢄꢄ
ꢅꢋꢁꢊꢄVꢄꢌꢁ+ꢆꢄ&+ & + ꢍꢆꢄꢃꢋꢃꢃꢄTꢄꢌꢅ+ꢆꢄ&+ ꢍꢆꢄꢂꢋꢊꢊꢄVꢄꢌꢀ+ꢆꢄ
ꢃꢉ+ꢍꢆꢄꢏꢋꢀꢇ±ꢏꢋꢃꢄꢌꢃ+ꢆꢄ& + ꢍꢆꢄꢏꢋꢏꢈ±ꢐꢋꢅꢈꢄꢌꢃ+ꢆꢄ+ ꢍꢆꢄ
ꢀꢀꢋꢏꢈꢄVꢄꢌꢀ+ꢆꢄ1+ꢍꢋꢄ)RXQGꢆꢄMꢓꢄ&ꢄꢏꢃꢋꢅꢇꢑꢄ+ꢄꢈꢋꢀꢁꢑꢄ1ꢄꢀꢀꢋꢇꢂꢋꢄ
& + 1 2 ꢋꢄ&DOFXODWHGꢆꢄMꢓꢄ&ꢄꢏꢃꢋꢏꢊꢑꢄ+ꢄꢈꢋꢀꢈꢑꢄ1ꢄꢀꢀꢋꢁꢐꢋꢄꢄ
7KLVꢄ VWXG\ꢄ ZDVꢄ SHUIRUPHGꢄ XQGHUꢄ ILQDQFLDOꢄ VXSSRUWꢄ
E\ꢄ WKHꢄ $VWDI¶HYꢄ .UDVQR\DUVNꢄ 6WDWHꢄ 3HGDJRJLFDOꢄ 8QLꢉ
YHUVLW\ꢄꢌSURMHFWꢄQRꢋꢄꢅꢃꢉꢇꢈꢉꢀ)ꢎ3ꢍꢋꢄ
5()(5(1&(6ꢄ
ꢁꢂ,VREXW\OꢂꢃꢂꢋꢁꢂPHWK\OSKHQ\ODPLQRꢌꢂꢄꢅꢆꢆꢂGLꢂ
K\GURꢂꢁ+ꢂDQWKUD>ꢆꢅꢇꢂG@>ꢆꢅꢇꢅꢁ@WULD]ROHꢂꢄꢅꢆꢆꢂGLRQHꢀꢀ
ꢇꢂR[LGHꢀ ꢋ,,,Gꢌꢉꢄ <LHOGꢄ ꢇꢋꢏꢈꢄ Jꢄ ꢌꢏꢇMꢍꢆꢄ PSꢄ ꢅꢇꢈ±ꢅꢇꢐƒ&ꢋꢄ
ꢀꢋꢄ*RUQRVWDHYꢆꢄ /ꢋ0ꢋꢆꢄ /HYGDQVNLLꢆꢄ 9ꢋ$ꢋꢆꢄ DQGꢄ )RNLQꢆꢄ (ꢋ3ꢋꢆꢄꢄ
ꢄ
=Kꢂꢀ2UJꢂꢀ.KLPꢋꢆꢄꢀꢊꢏꢊꢆꢄYROꢋꢄꢀꢈꢆꢄSꢋꢄꢀꢂꢊꢅꢋꢄ
ꢅꢋꢄ*RUQRVWDHYꢆꢄ/ꢋ0ꢋꢄDQGꢄ/HYGDQVNLLꢆꢄ9ꢋ$ꢋꢆꢄ=Kꢂꢀ2UJꢂꢀ.KLPꢋꢆꢄ
ꢀꢊꢐꢇꢆꢄYROꢋꢄꢀꢂꢆꢄSꢋꢄꢅꢅꢇꢊꢋꢄ
ꢁꢋꢄ$UQRO¶Gꢆꢄ (ꢋ9ꢋꢆꢄ /DYULNRYDꢆꢄ 7ꢋ,ꢋꢆꢄ DQGꢄ *RUQRVWDHYꢆꢄ /ꢋ0ꢋꢆꢄꢄ
=Kꢂꢀ2UJꢂꢀ.KLPꢋꢆꢄꢀꢊꢊꢁꢆꢄYROꢋꢄꢅꢊꢋꢄ
ꢃꢋꢄ*RUQRVWDHYꢆꢄ/ꢋ0ꢋꢄDQGꢄ/DYULNRYDꢆꢄ7ꢋ,ꢋꢆꢄ.KLPꢂꢀ*HWHURWVLNOꢂꢀ
6RHGLQꢋꢆꢄꢀꢊꢐꢁꢆꢄSꢋꢄꢀꢂꢅꢀꢋꢄ
ꢈꢋꢄ7DNDJLꢆꢄ .ꢋꢆꢄ 0L]XQRꢆꢄ $ꢋꢆꢄ ,ZDP RWRꢆꢄ +ꢋꢆꢄ 2RWDꢆꢄ 0ꢋꢆꢄꢄ
89ꢄ VSHFWUXPꢆꢄ
ꢄ ꢌORJ ꢍꢓꢄ ꢁꢃꢇꢄ ꢌꢃꢋꢀꢁꢍꢆꢄ ꢈꢈꢇꢄ ꢌꢁꢋꢐꢂꢍꢋꢄꢄ
ꢄ
+ꢄ105ꢄVSHFWUXPꢄꢌ&'&O ꢍꢆꢄ ꢆꢄSSPꢓꢄꢇꢋꢊꢈꢄGꢄ>ꢂ+ꢆꢄꢄ
ꢌ&+ ꢍ &+ꢆꢄ-ꢄ ꢄꢂꢄ+]@ꢆꢄꢅꢋꢅꢃꢄPꢄꢌꢀ+ꢆꢄ&+ꢍꢆꢄꢅꢋꢃꢇꢄVꢄꢌꢁ+ꢆꢄ
&+ & + ꢍꢆꢄ ꢃꢋꢇꢂꢄ Gꢄ ꢌꢅ+ꢆꢄ &+ ꢆꢄ -ꢄ ꢄ ꢂꢄ +]ꢍꢆꢄ ꢏꢋꢇꢈꢄ Vꢄ ꢌꢀ+ꢆꢄꢄ
ꢃꢉ+ꢍꢆꢄꢏꢋꢇꢇ±ꢏꢋꢃꢇꢄꢌꢃ+ꢆꢄ& + ꢍꢆꢄꢏꢋꢏ±ꢐꢋꢃꢇꢄꢌꢃ+ꢆꢄ+ ꢍꢆꢄ
ꢀꢀꢋꢈꢇꢄVꢄꢌꢀ+ꢆꢄ1+ꢍꢋꢄ)RXQGꢆꢄMꢓꢄ&ꢄꢂꢊꢋꢊꢐꢑꢄ+ꢄꢃꢋꢊꢈꢑꢄ1ꢄꢀꢅꢋꢈꢃꢋꢄ
& + 1 2 ꢋꢄ&DOFXODWHGꢆꢄMꢓꢄ&ꢄꢏꢇꢋꢃꢅꢑꢄ+ꢄꢈꢋꢀꢂꢑꢄ1ꢄꢀꢁꢋꢀꢃꢋꢄꢄ
ꢄ
ꢀ
ꢄ
6KLUDLꢆꢄ .ꢋꢆꢄ DQGꢄ 0DWVXRNDꢆꢄ 0ꢋꢆꢄ '\HVꢀ 3LJPHQWVꢆꢄ ꢅꢇꢇꢇꢆꢄꢄ
ꢁꢂ%XW\OꢂꢃꢂꢋꢍꢂPHWK\OSKHQ\ODPLQRꢌꢂꢄꢅꢆꢆꢂGLK\GURꢂ
ꢁ+ꢂDQWKUD>ꢆꢅꢇꢂG@>ꢆꢅꢇꢅꢁ@WULD]ROHꢂꢄꢅꢆꢆꢂGLRQHꢀ ꢇꢂR[LGHꢀ
ꢋ,,,Hꢌꢉꢄ<LHOGꢄꢇꢋꢏꢇꢄJꢄꢌꢂꢈMꢍꢆꢄPSꢄꢀꢊꢊ±ꢅꢇꢀƒ&ꢋꢄ89ꢄVSHFꢉ
ꢄ
YROꢋꢄꢃꢈꢆꢄSꢋꢄꢅꢇꢀꢋꢄ
ꢂꢋꢄ%XOJDNRYDꢆꢄ 1ꢋ$ꢋꢄ DQGꢄ *RUQRVWDHYꢆꢄ /ꢋ0ꢋꢆꢄ 5XVVꢂꢀ -ꢂꢀ 2UJꢂꢀ
&KHPꢋꢆꢄꢅꢇꢇꢀꢆꢄYROꢋꢄꢁꢏꢆꢄSꢋꢄꢀꢁꢈꢀꢋꢄ
ꢏꢋꢄ5DGDHYDꢆꢄ 1ꢋ<Xꢋꢆꢄ 'ROJXVKLQDꢆꢄ /ꢋ9ꢋꢆꢄ 6DNLOLGLꢆꢄ 9ꢋ7ꢋꢆꢄ DQGꢄ
ꢀ
WUXPꢆꢄ
ꢄꢌORJ ꢍꢓꢄꢁꢃꢇꢄꢌꢃꢋꢀꢃꢍꢆꢄꢈꢃꢈꢄꢌꢁꢋꢏꢊꢍꢋꢄ +ꢄ105ꢄ
VSHFWUXPꢄ ꢌ&'&O ꢍꢆꢄ ꢆꢄSSPꢓꢄ ꢇꢋꢊꢇꢄWꢄꢌꢁ+ꢆꢄ &+ &+ ꢍꢆꢄ
ꢀꢋꢁꢇ±ꢀꢋꢏꢈꢄꢌꢃ+ꢆꢄ&+ ꢍꢆꢄꢅꢋꢃꢇꢄVꢄꢌꢁ+ꢆꢄ&+ & + ꢍꢆꢄꢃꢋꢅꢈꢄWꢄ
ꢄ
ꢄ
*RUQRVWDHYꢆꢄ /ꢋ0ꢋꢆꢄ 5XVVꢂꢀ -ꢂꢀ 2UJꢂꢀ &KHPꢋꢆꢄ ꢅꢇꢇꢈꢆꢄ YROꢋꢄ ꢃꢀꢆꢄꢄ
Sꢋꢄꢊꢇꢏꢋꢄ
5866,$1ꢄꢄ-2851$/ꢄꢄ2)ꢄꢄ25*$1,&ꢄꢄ&+(0,675<ꢄꢄꢄ9ROꢋꢄꢄꢃꢅꢄꢄꢄ1Rꢋꢄꢄꢊꢄꢄꢄꢅꢇꢇꢂꢄ